Startseite Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
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Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2

  • Xiao-Hui Bai , Yan Xing und Si-Jie Liu ORCID logo EMAIL logo
Veröffentlicht/Copyright: 16. November 2021

Abstract

C13H9ClO2, monoclinic, P21 (No. 4), a = 6.5465(9) Å, b = 8.0647(11) Å, c = 10.8476(15) Å, β = 105.591(3)°, V = 551.63(13) Å3, Z = 2, R gt (F) = 0.0532, wR ref (F2) = 0.1507, T = 296(2) K.

CCDC no.: 2120367

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.25 × 0.20 × 0.18 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.33 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω-scans
θmax, completeness: 25°, >99%
N(hkl)measured, N(hkl)unique, Rint: 2796, 1690, 0.025
Criterion for Iobs, N(hkl)gt: Iobs > 2 σ(Iobs), 1253
N(param)refined: 146
Programs: Bruker programs [1], SHELX [2]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z Uiso*/Ueq
O1 0.8358 (7) 1.0726 (5) 0.5728 (4) 0.0618 (14)
H1 0.756229 1.146993 0.582516 0.093*
O2 0.6388 (8) 0.3264 (6) 0.6637 (5) 0.0735 (15)
Cl1 −0.0012 (3) 0.3639 (3) 1.04651 (18) 0.0822 (7)
C1 0.1700 (9) 0.3902 (8) 0.9494 (6) 0.0567 (17)
C2 0.1450 (10) 0.2919 (7) 0.8390 (6) 0.0609 (19)
H2 0.038138 0.212591 0.818033 0.073*
C3 0.2789 (10) 0.3140 (7) 0.7628 (6) 0.0532 (16)
H3 0.264049 0.248080 0.690608 0.064*
C4 0.4361 (9) 0.4334 (7) 0.7923 (6) 0.0491 (16)
C5 0.4599 (10) 0.5292 (7) 0.9022 (6) 0.0539 (17)
H5 0.565132 0.609892 0.922246 0.065*
C6 0.3283 (10) 0.5058 (8) 0.9823 (7) 0.0586 (18)
H6 0.347685 0.567569 1.056967 0.070*
C7 0.5786 (9) 0.4515 (8) 0.7077 (6) 0.0512 (16)
C8 0.6442 (9) 0.6177 (8) 0.6756 (6) 0.0486 (15)
C9 0.8213 (10) 0.6349 (8) 0.6281 (6) 0.0530 (17)
H9 0.898507 0.541350 0.618271 0.064*
C10 0.8825 (10) 0.7867 (9) 0.5959 (6) 0.0534 (17)
H10 1.002962 0.796166 0.566481 0.064*
C11 0.7668 (9) 0.9266 (8) 0.6068 (5) 0.0459 (15)
C12 0.5876 (9) 0.9116 (8) 0.6493 (6) 0.0496 (15)
H12 0.506712 1.004984 0.654059 0.059*
C13 0.5277 (9) 0.7598 (7) 0.6846 (6) 0.0462 (15)
H13 0.407997 0.751506 0.714936 0.055*

Source of material

All chemical solvents and reagents are purchased and used without further purification. A mixture of thiophene-2-carbohydrazide (1 mmol, 142.2 mg) and 4-chloro-4′-hydroxybenzophenone (1 mmol, 232.7 mg) in anhydrous ethanol (10 mL) containing a few drops of glacial acetic acid, was refluxed for 2 h, then filtered, left quietly, and evaporated naturally. After three days, colorless block crystals of 4-chloro-4′-hydroxybenzophenone were obtained unexpectedly.

Experimental details

All H atoms were included in calculated positions and refined as riding atoms, with C–H = 0.93 Å and O–H = 0.82 Å. The Uiso values were set to be 1.5Ueq(O) and 1.2Ueq(C).

Discussion

As a class of important organic compounds, phenylmethanones have various biological activities such as antifungal, antiinflammatory, antibacterial, and anticancer activities [3], [4], [5], [6], [7], [8], [9], [10]. Different substituents in the benzophenone nucleus are essential in investigation of the quantitative structure-activity relationships.

The asymmetric unit of the title compound consists of one formula unit (cf. the figure). Crystal determination exhibits that the title compound is monoclinic, P21 (No. 4), a = 6.5465(9) Å, b = 8.0647(11) Å, c = 10.8476(15) Å, β = 105.591(3)°, V = 551.63(13) Å3, and Z = 2, which is different from the previously reported the structure of 4-chloro-4′-hydroxybenzophenone determined at 120(2) K, in which of orthorhombic space group Pca21 (No. 29) with a = 23.3058(11) Å, b = 5.5770(2) Å, c = 8.2847(4) Å, V = 1076.82(8) Å3, and Z = 4 [10]. In the crystal structure, the short distance d(C7–O2) = 1.225(8) Å exhibits a typical C=O double bond which is not affected by hydrogen bonding. The distance d(C11–O1) = 1.347(7) Å shows a typical C–O single bond. The dihedral angle formed by the two aromatic rings is 55.55(1)°, which is quite different from the literature known structure of 64.66(8)° [10]. In the crystal structure, the molecules are linked into one-dimensional chains along the b-axis direction by O–H⃛O hydrogen bonds.


Corresponding author: Si-Jie Liu, College of Chemical Engineering, Shijiazhuang University, 050035, Shijiazhuang, Hebei, People’s Republic of China, E-mail: .

Funding source: Research Project of Yulin Science and Technology Bureau

Award Identifier / Grant number: 2019-83-3

Award Identifier / Grant number: 2019-83-5

Funding source: Natural Science Youth Foundation of Hebei Province

Award Identifier / Grant number: H2018106015

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This work was financial supported by Research Project of Yulin Science and Technology Bureau (2019-83-3 and 2019-83-5) and Natural Science Youth Foundation of Hebei Province (H2018106015).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2021-10-14
Accepted: 2021-11-05
Published Online: 2021-11-16
Published in Print: 2022-02-23

© 2021 Xiao-Hui Bai et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-3-yl)methylene)-3, 4-dihydronaphthalen-1(2H)-one, C17H15NO3
  4. Crystal structure of (E)-7-methoxy-2-((2-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1 (2H)-one, C18H17NO3
  5. The crystal structure of N 6,N 6′-di(pyridin-2-yl)-[2,2′-bipyridine]-6,6′-diamine, C20H16N6
  6. The crystal structure of {N 1,N 2-bis[2,4-dimethyl-6-(4-(tert-butyl)phenyl)(phenyl)methyl]acenaphthylene-1,2-diimino-κ2 N, N′}-dibromido-nickel(II) – dichloromethane(1/2), C64H64Br2Cl4N2Ni
  7. Synthesis and crystal structure of nonacarbonyltris[(2-thia-1,3,5-triaza-7-phosphatricylco[3.3.1.1]decane-κ1 P)-2,2-dioxide]triruthenium(0) – acetonitrile (7/6), C25.71H32.57N9.86O15P3S3Ru3
  8. A new polymorph of 1-(4-nitrophenyl)-1H-benzimidazole (C13H9N3O2)
  9. The crystal structure of 2,2′-((1E,1′E)-(naphthalene-2,3 diylbis(azanylylidene)) bis(methanylylidene))bis(4-methylphenol), C26H22N2O2
  10. The crystal structure of bis(μ2-iodido)-bis(η6-benzene)-bis(iodido)-diosmium(II), C12H12I4Os2
  11. Redetermination of the crystal structure of bis{hydridotris(3,5-dimethylpyrazol-1-yl-κN 3)borato}copper(II), C30H44B2CuN12
  12. Crystal structure of (E)-3-((4-(tert-butyl)phenyl)thio)-4-hydroxypent-3-en-2-one, C15H20O2S
  13. Crystal structure of 2,2′-(p-tolylazanediyl)bis(1-phenylethan-1-one), C23H21NO2
  14. Redetermination of the crystal structure of the crystal sponge the poly[tetrakis(μ3-2,4,6-tris(pyridin-4-yl)-1,3,5-triazine)-dodecaiodidohexazinc(II) nitrobenzene solvate], C72H48I12N24Zn6⋅10(C6H5NO2)
  15. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(6-methylpyridin-2-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C44H45N5O2
  16. Crystal structure of (E)-7-fluoro-2-(3-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C17H12F2O1
  17. Crystal structure of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea (1/2)
  18. Crystal structure of [2,2′-{azanediyl)bis[(propane-3,1-diyl)(azanylylidene)methylylidene]} bis(3,5-dichlorophenolato)-κ2O,O′]-isothiocyanato-κN-iron(III), C21H19Cl4FeN4O2S
  19. Crystal structure of (4-chlorophenyl)(4-hydroxyphenyl)methanone, C13H9ClO2
  20. Crystal structure of 6,6′-((pentane-1,3-diylbis(azaneylylidene))bis(methaneylylidene))bis(2,4-dibromolphenolato-κ4 N,N′,O,O′)copper(II),) C19H16Br4CuN2O2
  21. Chlorido-(2,2′-(ethane-bis(5-methoxyphenolato))-κ4 N,N,O,O′)manganese(III) monohydrate, C19H18Cl2CuN2O2
  22. Crystal structure of 2,6-di-tert-butyl-4-(4-methoxybenzylidene)cyclohexa-2,5-dien-1-one, C22H28O2
  23. Crystal structure of [6,6′-(((2,2-dimethylpropane-1,3-diyl)bis(azanylylidene))bis(methanylylidene))bis(2-chlorophenolato)-κ4N,N′,O,O′]copper(II)
  24. Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
  25. Crystal structure of bis{hydridotris(3-trifluoromethyl-5-methylpyrazolyl-1-yl)borato-κN 3}manganese(II), C30H26B2F18MnN12
  26. Crystal structure of 1-(2-methylphenyl)-2-(2-methylbenzo[b]thienyl)-3,3,4,4,5,5-hexafluorocyclopent-ene, C21H14F6S
  27. Crystal structure of 2-(3-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  28. Crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium chloride – chloroform (1/1), C21H23Cl4I2N3
  29. Crystal structure of azido-k1 N-{6,6′-((((methylazanediyl)bis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))bis(2,4-dibromophenolato)k5 N,N′,N″,O,O′}cobalt(III)-methanol (1/1)), C21H23Br4CoN6O3
  30. The crystal structure of 2-(4-((carbamimidoylthio)methyl)benzyl)isothiouronium hexafluorophosphate monohydrate, C10H17F6N4OPS2
  31. Crystal structure of 1,1′-(methane-1,1-diyl)bis(3-methyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C9H14F12N4P2
  32. Crystal structure of (4′E)-6′-(diethylamino)-2-[(E)-[(pyren-1-yl)methylidene]amino]-4′-{2-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidene]ethylidene}-1′,2,2′,3,3′,4′-hexahydrospiro[isoindole-1,9′-xanthene]-3-one, C54H48N4O2
  33. Crystal structure of poly[bis(μ2-2,6-bis(1-imidazoly)pyridine-κ2 N,N′)-bis(thiocyanato-κ1 N)copper(II)] dithiocyanate, C24H18CuN12S2
  34. Cones with a three-fold symmetry constructed from three hydrogen bonded theophyllinium cations that coat [FeCl4] anions in the crystal structure of tris(theophyllinium) bis(tetrachloridoferrate(III)) chloride trihydrate, C21H33Cl9Fe2N12O9
  35. Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
  36. The crystal structure of (E)-3-chloro-2-(2-(4-methylbenzylidene)hydrazinyl)pyridine, C13H12ClN3
  37. The crystal structure of 4-phenyl-4-[2-(pyridine-4-carbonyl)hydrazinylidene]butanoic acid, C16H15N3O3
  38. The crystal structure of 6-amino-5-carboxypyridin-1-ium pentaiodide monohydrate C6H9I5N2O3
  39. Crystal structure of bis(μ3-oxido)-bis(μ2-2-formylbenzoato-k2O:O′)-bis(2-(dimethoxymethyl)-benzoato-κO)-oktakismethyl-tetratin(IV)
  40. Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
  41. Crystal structure of (E)-amino(2-((5-methylfuran-2-yl)methylene)hydrazinyl) methaniminium nitrate monohydrate, C14H26N10O10
  42. The crystal structure of N′-(2-chloro-6-hydroxybenzylidene)thiophene-2-carbohydrazide monohydrate, C12H11ClN2O3S
  43. Crystal structure of catena-poly[(μ2-1,1′-(biphenyl-4,4-diyl)bis(1H-imidazol)-κ2N:N′)-bis(4-bromobenzoate-κ1O)zinc(II)], C64H44Br4N8O8Zn2
  44. The crystal structure of catena-poly[(1-(4-carboxybenzyl)pyridin-1-ium-4-carboxylato-κ1O)-(μ2-oxalato-κ4 O:O′:O″:O‴)dioxidouranium(VI)], C16H11NO10U
  45. Crystal structure of 3-allyl-4-(2-bromoethyl)-5-(4-methoxyphenyl)-2-phenylfuran, C22H21BrO2
  46. Halogen bonds in the crystal structure of 4,3′:5′,4″-terpyridine — 1,3-diiodotetrafluorobenzene (1/1), C21H11F4I2N3
  47. Crystal structure of 2-(1H-indol-3-yl)ethan-1-aminium 2-(4-acetylphenoxy)acetate, C20H22N2O4
  48. Chalcogen bonds in the crystal structure of 4,7-dibromo-2,1,3-benzoselenadiazole, C6H2Br2N2Se
  49. The crystal structure of 1,4-bis((1H-benzimidazol-2-yl)methyl)-piperazine-2,5-dione dihydrate, C20H22N6O4
  50. The crystal structure of C19H20O8
  51. The crystal structure of KNa3Te8O18·5H2O exhibiting a 2[Te4O9]2− layer
  52. Erratum
  53. Erratum to: Crystal structure of (Z)-3-(6-bromo-1H-indol-3-yl)-1,3-diphenylprop-2-en-1-one, C23H16BrNO
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